Synthesis of 4-nitrobenzoyl chloride

Preparation of 4-nitrobenzoyl chloride

Preparation of 4-nitrobenzoyl chloride

Preparation of 4-nitrobenzoyl chloride

20 g of 4-nitrobenzoic acid and 25 g of phosphorus pentachloride are mixed in a 250-ml flask fitted with a reflux air condenser in a fume cupboard. The flask is heated on a water bath with occasional shaking until the evolution of hydrogen chloride nearly ceases and a clear homogeneous liquid is obtained. The reaction product is transferred to a distilling flask and distilled up to 220° C to remove phosphorus oxychloride. The residue of 4-nitrobenzoyl chloride may be purified by crystallisation from carbon tetrachloride or, by distillation under reduced pressure b.p. 155°C/20mm. Yield 90%, yellow needles; m.p. 73°C.

Systematic organic chemistry, by W. M. Cumming, 333, 1937.

IUPAC Name

4-nitrobenzoyl chloride

InChI

InChI=1S/C7H4ClNO3/c8-7(10)5-1-3-6(4-2-5)9(11)12/h1-4H

InChI Key

SKDHHIUENRGTHK-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1C(=O)Cl)[N+](=O)[O-]

MeSH Synonyms

4-nitrobenzoyl chloride, p-nitrobenzoyl chloride

Depositor-Supplied Synonyms

4-Nitrobenzoyl chloride, 122-04-3, P-NITROBENZOYL CHLORIDE, Benzoyl chloride, 4-nitro-, Benzoyl chloride, p-nitro-, p-Nitrobenzoic acid chloride, 4-Nitrobenzoic acid chloride, 4-Nitro-benzoyl chloride, Nitrobenzoyl chloride, 4-, CCRIS 3136, SKDHHIUENRGTHK-UHFFFAOYSA-N, NSC 5381, EINECS 204-517-4, BRN 0473192, AI3-08914, p-nitrobenzoylchloride, 4-nitrobenzoylchloride, p-nitro-benzoylchloride, 4-nitro-benzoylchloride, 4-nitrobenzoyi chloride, PubChem22042, paranitrobenzoyl chloride, ACMC-1BPGC, p-nitro-benzoyl chloride, 4 -nitrobenzoyl chloride, 4-nitro benzoyl chloride, 4-nitro-benzoyl-chloride, AC1Q1XHS, 4–Nitrobenzoyl chloride, para-nitrobenzoyl chloride, p-nitro- benzoyl chloride, DSSTox_CID_5742, UNII-X3H8PW2GC4, AC1L1R4V, DSSTox_RID_77903, X3H8PW2GC4, DSSTox_GSID_25742, SCHEMBL43141, KSC176O4P, 4-(Chlorocarbonyl)nitrobenzene, 112208_ALDRICH, CHEMBL1599838, 73120_FLUKA, 73122_FLUKA, CTK0H6747, NSC5381, MolPort-001-779-784, BB_SC-6997, ACN-S002288, NSC-5381, STR01076, ZINC1680883, Tox21_200137, ANW-17933, BBL012202, LS-661, SBB056880, STL163544, ZINC01680883, AKOS005716884, MCULE-7189136630, RP24558, RTR-003559, TRA0056714, NCGC00091803-01, NCGC00091803-02, NCGC00257691-01, AN-22864, BC225488, CAS-122-04-3, CJ-27654, KB-40084, OR025202, AB1006760, TL8000585, TR-003559, FT-0619215, N0176, ST50983988, 22202-EP2301939A1, 22202-EP2305682A1, 22202-EP2308879A1, 22202-EP2314593A1, 4-09-00-01191 (Beilstein Handbook Reference), A804833, S01-0562, W-108439, 3B3-033634, InChI=1/C7H4ClNO3/c8-7(10)5-1-3-6(4-2-5)9(11)12/h1-4, P-NITROBENZOYL CHLORIDE (SEE ALSO: P-NITROBENZOIC ACID (CAS 62-23-7))

Removed Synonyms

null, PHENYLACETYL CHLORIDE, CID8502

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